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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o114
doi:10.1107/S1600536814000026

16-Oxa­penta­cyclo­[6.6.5.01,18.02,7.09,14]nona­deca-2,4,6,9,11,13,18-heptaen-15-one

Eason M. Mathew,a M. Sithambaresan,b* P. A. Unnikrishnana and M. R. Prathapachandra Kurupa

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Chenkalady, Sri Lanka
*Correspondence e-mail: eesans@yahoo.com

(Received 15 December 2013; accepted 1 January 2014; online 8 January 2014)

In the title compound, C18H12O2, the benzene rings are inclined to one another by 66.79 (7)°. The five-membered ring is almost planar with a maximum deviation of 0.014 (1) Å. In the crystal, the mol­ecules are linked by pairs of weak C—H⋯O interactions into centrosymmetric dimers. These dimers are linked by C—H⋯π interactions, forming a three-dimensional structure.

CCDC reference: 979286

Related literature

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010[Khalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353-1360.]); Cox et al. (2013[Cox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640-643.]). For the synthesis of related compounds, see: Ciganek (1980[Ciganek, E. (1980). J. Org. Chem. 45, 1497-1505.]); De Luca et al. (2001[De Luca, L., Giacomelli, G. & Taddei, M. (2001). J. Org. Chem. 66, 2534-2537.]). For a related structure, see: Mathew et al. (2013[Mathew, E. M., Sithambaresan, M., Unnikrishnan, P. A. & Kurup, M. R. P. (2013). Acta Cryst. E69, o1165.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C18H12O2

  • Mr = 260.28

  • Monoclinic, P 21 /c

  • a = 9.351 (1) Å

  • b = 13.8153 (16) Å

  • c = 10.1514 (9) Å

  • β = 105.295 (4)°

  • V = 1265.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.40 × 0.35 × 0.30 mm
Data collection

  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.974

  • 9570 measured reflections

  • 3123 independent reflections

  • 2224 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.132

  • S = 1.03

  • 3123 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯Cg1i 0.98 2.92 3.7835 (16) 148
C16—H16B⋯Cg1ii 0.97 2.76 3.650 (2) 153
C18—H18⋯Cg2i 0.93 2.84 3.3942 (16) 120
C3—H3⋯O1iii 0.93 2.64 3.519 (2) 157
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 979286

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S1600536814000026/yk2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000026/yk2102Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000026/yk2102Isup3.cml

checkCIF report


Comment top

Dibenzobarrelene derivatives have been used as the key intermediates in the synthesis of several compounds which show various biological activities. Besides, they have showed application in drug development for various diseases (Khalil et al., 2010) and in the alignment of nematic liquid crystals (Cox et al., 2013). As a continuous work on the dibenzobarrelene compounds, a new dibenzobarrelene derivative, 3,5-dihydro-5,9 b-o-benzonaphtho [1,2-c] furan-1-one, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.

The compound crystallizes in monoclinic space group P21/c. The dihedral angle of the two aromatic rings of the anthracene moiety is 66.79 (7)°. The five-membered heterocyclic ring C14–17/O2 is almost planar with a maximum deviation of 0.014 (1)° for C14 carbon atom in the ring. One of the fused six-membered ring of the molecule C5—C8/C13/C14 is in boat conformation [φ = 117.52 (10)° and θ = 90.62 (10)°] having total puckering amplitude QT of 0.8495 (15) Å. The other six-membered ring C5—C7/C14/C17/C18 is also in boat conformation [φ = 302.45 (11)° and θ = 89.63 (12)°] having total puckering amplitude QT of 0.7919 (15) Å. Another six-membered ring C7/C8/C13/C14/C17/C18 is also in the same conformation [φ = 181.09 (11)° and θ = 90.35 (11)°] having total puckering amplitude QT of 0.7915 (15) Å (Cremer & Pople, 1975).

Three C–H···π interactions (Fig. 2) are found in the molecule. Whilst the two C–H···π interactions exist between the H atoms attached at the C7 and C16 atoms and the aromatic rings (C1—C6) of the anthracene moiety of two adjacent molecules from opposite sides of the main molecule, the third C–H···π interaction exists between the hydrogen at C18 atom and the C8—C13 ring of one of the above neighbouring molecules respectively with H···π distances of 2.92, 2.76 and 2.84 Å (Table 1). There are very weak π···π interactions between the aromatic rings of the anthracene moiety with centroid-centroid distances greater than 4 Å. However, packing of molecules is predominantly favored by the C–H···π interactions. Similar intermolecular interactive behaviour was found in the compound 8-phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18- heptane (Mathew et al., 2013). Fig. 3 shows the packing diagram of the title compound along a axis.

Related literature top

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010); Cox et al. (2013). For the synthesis of related compounds, see: Ciganek (1980); De Luca et al. (2001). For related structure, see: Mathew et al. (2013). For puckering analysis, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared by adapting a reported procedure (Ciganek, 1980; De Luca et al., 2001). Triethylamine (0.70 ml, 5 mmol) was added to a solution of 9-anthracene carboxylic acid (1.11 g, 5 mmol) and cyanuric chloride (0.92 g, 5 mmol) in acetone and stirred at room temperature for 1 h to obtain 9-anthracene acid chloride. Propargyl alcohol (0.30 ml, 5 mmol) was added to it and the mixture was stirred for 4 h. Propargyl-9-anthroate obtained was purified by silica gel column chromatography using a mixture of hexane and dichloromethane as eluents. Propargyl-9-anthroate was refluxed in 10 ml of p-xylene for 48 h (intramolecular Diels-Alder reaction) to generate the title compound. Colourless crystals acceptable for X-ray structure determination were recrystallized from acetonitrile by slow evaporation over a few days (m.p: 260 °C).

Refinement top

All H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances 0.93–0.97 Å. H atoms were assigned as Uiso=1.2Ueq. Omitted owing to bad disagreement were the reflections (1 0 0).

Structure description top

Dibenzobarrelene derivatives have been used as the key intermediates in the synthesis of several compounds which show various biological activities. Besides, they have showed application in drug development for various diseases (Khalil et al., 2010) and in the alignment of nematic liquid crystals (Cox et al., 2013). As a continuous work on the dibenzobarrelene compounds, a new dibenzobarrelene derivative, 3,5-dihydro-5,9 b-o-benzonaphtho [1,2-c] furan-1-one, was prepared and structurally characterized. The ORTEP view of the title compound is shown in Fig. 1.

The compound crystallizes in monoclinic space group P21/c. The dihedral angle of the two aromatic rings of the anthracene moiety is 66.79 (7)°. The five-membered heterocyclic ring C14–17/O2 is almost planar with a maximum deviation of 0.014 (1)° for C14 carbon atom in the ring. One of the fused six-membered ring of the molecule C5—C8/C13/C14 is in boat conformation [φ = 117.52 (10)° and θ = 90.62 (10)°] having total puckering amplitude QT of 0.8495 (15) Å. The other six-membered ring C5—C7/C14/C17/C18 is also in boat conformation [φ = 302.45 (11)° and θ = 89.63 (12)°] having total puckering amplitude QT of 0.7919 (15) Å. Another six-membered ring C7/C8/C13/C14/C17/C18 is also in the same conformation [φ = 181.09 (11)° and θ = 90.35 (11)°] having total puckering amplitude QT of 0.7915 (15) Å (Cremer & Pople, 1975).

Three C–H···π interactions (Fig. 2) are found in the molecule. Whilst the two C–H···π interactions exist between the H atoms attached at the C7 and C16 atoms and the aromatic rings (C1—C6) of the anthracene moiety of two adjacent molecules from opposite sides of the main molecule, the third C–H···π interaction exists between the hydrogen at C18 atom and the C8—C13 ring of one of the above neighbouring molecules respectively with H···π distances of 2.92, 2.76 and 2.84 Å (Table 1). There are very weak π···π interactions between the aromatic rings of the anthracene moiety with centroid-centroid distances greater than 4 Å. However, packing of molecules is predominantly favored by the C–H···π interactions. Similar intermolecular interactive behaviour was found in the compound 8-phenyl-16-thiapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18- heptane (Mathew et al., 2013). Fig. 3 shows the packing diagram of the title compound along a axis.

For background to dibenzobarrelene dervatives and their applications, see: Khalil et al. (2010); Cox et al. (2013). For the synthesis of related compounds, see: Ciganek (1980); De Luca et al. (2001). For related structure, see: Mathew et al. (2013). For puckering analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title molecule drawn with 50% probability displacement ellipsoids and showing the atom labelling scheme.
[Figure 2] Fig. 2. C—H···π interactions in the title compound.
[Figure 3] Fig. 3. Packing diagram of the compound along a axis.
16-Oxapentacyclo[6.6.5.01,18.02,7.09,14]nonadeca-2,4,6,9,11,13,18-heptaen-15-one top
Crystal data top
C18H12O2F(000) = 544
Mr = 260.28Dx = 1.367 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2538 reflections
a = 9.351 (1) Åθ = 2.7–27.2°
b = 13.8153 (16) ŵ = 0.09 mm−1
c = 10.1514 (9) ÅT = 296 K
β = 105.295 (4)°Block, colourless
V = 1265.0 (2) Å30.40 × 0.35 × 0.30 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		3123 independent reflections
Radiation source: fine-focus sealed tube2224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.7°
ω and φ scanh = −12→12
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		k = −18→18
Tmin = 0.966, Tmax = 0.974l = −9→13
9570 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.132 w = 1/[σ2(Fo2) + (0.0716P)2 + 0.0884P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3123 reflectionsΔρmax = 0.22 e Å−3
182 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (4)
Crystal data top
C18H12O2V = 1265.0 (2) Å3
Mr = 260.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.351 (1) ŵ = 0.09 mm−1
b = 13.8153 (16) ÅT = 296 K
c = 10.1514 (9) Å0.40 × 0.35 × 0.30 mm
β = 105.295 (4)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer		3123 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		2224 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.974Rint = 0.035
9570 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å−3
3123 reflectionsΔρmin = −0.19 e Å−3
182 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.80024 (14)−0.01503 (9)0.22190 (12)0.0570 (4)
O20.81229 (15)−0.05665 (8)0.43556 (13)0.0590 (4)
C10.35542 (16)0.23405 (12)0.28342 (15)0.0410 (4)
H10.31880.28690.32090.049*
C20.27224 (16)0.19194 (12)0.16350 (15)0.0454 (4)
H20.17990.21750.11980.054*
C30.32484 (18)0.11291 (12)0.10856 (15)0.0440 (4)
H30.26630.08400.03000.053*
C40.46477 (17)0.07589 (11)0.16959 (13)0.0368 (3)
H40.50100.02300.13180.044*
C50.54912 (15)0.11890 (10)0.28707 (13)0.0294 (3)
C60.49305 (15)0.19640 (10)0.34614 (13)0.0323 (3)
C70.59990 (16)0.23295 (11)0.47731 (13)0.0372 (4)
H70.55840.28580.52010.045*
C80.73588 (15)0.26293 (10)0.43345 (13)0.0329 (3)
C90.79945 (18)0.35413 (11)0.44610 (15)0.0426 (4)
H90.76270.40330.49050.051*
C100.91836 (18)0.37120 (12)0.39195 (16)0.0472 (4)
H100.96150.43230.40010.057*
C110.97316 (17)0.29906 (12)0.32652 (16)0.0462 (4)
H111.05190.31200.28930.055*
C120.91213 (15)0.20649 (11)0.31525 (14)0.0373 (3)
H120.95030.15730.27200.045*
C130.79444 (14)0.18928 (10)0.36931 (12)0.0297 (3)
C140.70748 (15)0.09493 (10)0.36761 (13)0.0298 (3)
C150.77607 (17)0.00483 (11)0.32910 (16)0.0408 (4)
C160.7720 (2)−0.01959 (13)0.55478 (17)0.0566 (5)
H16A0.8592−0.01260.63110.068*
H16B0.7028−0.06290.58130.068*
C170.70234 (16)0.07596 (12)0.51340 (14)0.0375 (3)
C180.64493 (17)0.14591 (12)0.57090 (14)0.0419 (4)
H180.63310.14260.65890.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0749 (9)0.0426 (7)0.0586 (7)0.0140 (6)0.0266 (6)−0.0097 (6)
O20.0767 (9)0.0353 (7)0.0645 (8)0.0168 (6)0.0177 (6)0.0126 (6)
C10.0341 (8)0.0432 (9)0.0454 (8)0.0049 (6)0.0097 (6)−0.0012 (7)
C20.0322 (8)0.0528 (10)0.0457 (8)−0.0005 (7)0.0005 (7)0.0072 (7)
C30.0429 (8)0.0487 (10)0.0339 (7)−0.0133 (7)−0.0015 (6)0.0007 (7)
C40.0452 (8)0.0319 (7)0.0332 (7)−0.0058 (6)0.0099 (6)−0.0028 (6)
C50.0327 (7)0.0288 (7)0.0268 (6)−0.0021 (5)0.0079 (5)0.0025 (5)
C60.0311 (7)0.0355 (8)0.0304 (6)−0.0006 (5)0.0085 (5)0.0000 (6)
C70.0383 (8)0.0412 (8)0.0311 (7)0.0048 (6)0.0076 (6)−0.0096 (6)
C80.0330 (7)0.0337 (7)0.0276 (6)0.0023 (6)0.0003 (5)−0.0045 (5)
C90.0451 (9)0.0339 (8)0.0396 (8)0.0026 (6)−0.0049 (7)−0.0080 (6)
C100.0407 (9)0.0386 (9)0.0532 (9)−0.0103 (7)−0.0035 (7)0.0001 (7)
C110.0296 (7)0.0513 (10)0.0542 (9)−0.0062 (6)0.0051 (7)0.0080 (8)
C120.0292 (7)0.0400 (8)0.0417 (7)0.0033 (6)0.0073 (6)0.0026 (6)
C130.0295 (7)0.0289 (7)0.0279 (6)0.0029 (5)0.0026 (5)0.0007 (5)
C140.0337 (7)0.0271 (7)0.0286 (6)0.0017 (5)0.0080 (5)0.0002 (5)
C150.0437 (8)0.0306 (8)0.0477 (8)0.0037 (6)0.0111 (7)−0.0007 (7)
C160.0646 (11)0.0535 (11)0.0507 (9)0.0097 (9)0.0136 (9)0.0200 (8)
C170.0371 (8)0.0429 (8)0.0307 (7)0.0001 (6)0.0056 (6)0.0074 (6)
C180.0426 (8)0.0582 (10)0.0251 (6)−0.0012 (7)0.0092 (6)0.0013 (6)
Geometric parameters (Å, º) top
O1—C151.2001 (19)C8—C91.385 (2)
O2—C151.3457 (19)C8—C131.3955 (19)
O2—C161.452 (2)C9—C101.384 (2)
C1—C61.3783 (19)C9—H90.9300
C1—C21.388 (2)C10—C111.370 (2)
C1—H10.9300C10—H100.9300
C2—C31.375 (2)C11—C121.393 (2)
C2—H20.9300C11—H110.9300
C3—C41.389 (2)C12—C131.374 (2)
C3—H30.9300C12—H120.9300
C4—C51.3788 (19)C13—C141.5339 (19)
C4—H40.9300C14—C151.499 (2)
C5—C61.395 (2)C14—C171.5163 (18)
C5—C141.5272 (18)C16—C171.483 (2)
C6—C71.5246 (18)C16—H16A0.9700
C7—C81.512 (2)C16—H16B0.9700
C7—C181.521 (2)C17—C181.315 (2)
C7—H70.9800C18—H180.9300
C15—O2—C16112.40 (12)C11—C10—H10119.6
C6—C1—C2119.08 (15)C9—C10—H10119.6
C6—C1—H1120.5C10—C11—C12120.68 (15)
C2—C1—H1120.5C10—C11—H11119.7
C3—C2—C1120.74 (14)C12—C11—H11119.7
C3—C2—H2119.6C13—C12—C11118.69 (14)
C1—C2—H2119.6C13—C12—H12120.7
C2—C3—C4120.47 (13)C11—C12—H12120.7
C2—C3—H3119.8C12—C13—C8120.96 (13)
C4—C3—H3119.8C12—C13—C14128.37 (12)
C5—C4—C3118.93 (14)C8—C13—C14110.66 (12)
C5—C4—H4120.5C15—C14—C17103.71 (12)
C3—C4—H4120.5C15—C14—C5117.50 (11)
C4—C5—C6120.55 (13)C17—C14—C5106.50 (11)
C4—C5—C14128.48 (13)C15—C14—C13116.53 (12)
C6—C5—C14110.95 (11)C17—C14—C13106.81 (11)
C1—C6—C5120.13 (13)C5—C14—C13104.96 (10)
C1—C6—C7126.55 (14)O1—C15—O2121.07 (14)
C5—C6—C7113.29 (11)O1—C15—C14128.49 (14)
C8—C7—C18106.55 (12)O2—C15—C14110.44 (13)
C8—C7—C6104.00 (11)O2—C16—C17105.60 (12)
C18—C7—C6107.06 (12)O2—C16—H16A110.6
C8—C7—H7112.9C17—C16—H16A110.6
C18—C7—H7112.9O2—C16—H16B110.6
C6—C7—H7112.9C17—C16—H16B110.6
C9—C8—C13119.68 (14)H16A—C16—H16B108.8
C9—C8—C7126.58 (14)C18—C17—C16136.81 (14)
C13—C8—C7113.68 (12)C18—C17—C14115.35 (13)
C10—C9—C8119.23 (14)C16—C17—C14107.80 (13)
C10—C9—H9120.4C17—C18—C7112.45 (12)
C8—C9—H9120.4C17—C18—H18123.8
C11—C10—C9120.73 (15)C7—C18—H18123.8
C6—C1—C2—C30.9 (2)C4—C5—C14—C17−125.40 (15)
C1—C2—C3—C4−2.3 (2)C6—C5—C14—C1756.01 (15)
C2—C3—C4—C50.8 (2)C4—C5—C14—C13121.57 (15)
C3—C4—C5—C62.0 (2)C6—C5—C14—C13−57.03 (14)
C3—C4—C5—C14−176.46 (13)C12—C13—C14—C1513.99 (19)
C2—C1—C6—C51.9 (2)C8—C13—C14—C15−167.52 (11)
C2—C1—C6—C7179.78 (14)C12—C13—C14—C17129.29 (14)
C4—C5—C6—C1−3.4 (2)C8—C13—C14—C17−52.22 (14)
C14—C5—C6—C1175.29 (12)C12—C13—C14—C5−117.89 (14)
C4—C5—C6—C7178.45 (12)C8—C13—C14—C560.60 (13)
C14—C5—C6—C7−2.83 (17)C16—O2—C15—O1−179.23 (15)
C1—C6—C7—C8−118.49 (16)C16—O2—C15—C141.30 (19)
C5—C6—C7—C859.48 (15)C17—C14—C15—O1178.30 (16)
C1—C6—C7—C18128.95 (16)C5—C14—C15—O161.1 (2)
C5—C6—C7—C18−53.07 (16)C13—C14—C15—O1−64.7 (2)
C18—C7—C8—C9−125.80 (15)C17—C14—C15—O2−2.28 (16)
C6—C7—C8—C9121.28 (15)C5—C14—C15—O2−119.45 (14)
C18—C7—C8—C1357.06 (14)C13—C14—C15—O2114.75 (14)
C6—C7—C8—C13−55.86 (15)C15—O2—C16—C170.30 (19)
C13—C8—C9—C101.4 (2)O2—C16—C17—C18−178.90 (18)
C7—C8—C9—C10−175.55 (13)O2—C16—C17—C14−1.73 (17)
C8—C9—C10—C110.0 (2)C15—C14—C17—C18−179.75 (13)
C9—C10—C11—C12−1.2 (2)C5—C14—C17—C18−55.14 (16)
C10—C11—C12—C130.9 (2)C13—C14—C17—C1856.61 (16)
C11—C12—C13—C80.5 (2)C15—C14—C17—C162.39 (16)
C11—C12—C13—C14178.84 (12)C5—C14—C17—C16127.00 (13)
C9—C8—C13—C12−1.7 (2)C13—C14—C17—C16−121.24 (13)
C7—C8—C13—C12175.68 (11)C16—C17—C18—C7175.33 (18)
C9—C8—C13—C14179.70 (11)C14—C17—C18—C7−1.69 (19)
C7—C8—C13—C14−2.94 (15)C8—C7—C18—C17−54.71 (16)
C4—C5—C14—C15−9.8 (2)C6—C7—C18—C1756.09 (17)
C6—C5—C14—C15171.65 (12)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7···Cg1i0.982.923.7835 (16)148
C16—H16B···Cg1ii0.972.763.650 (2)153
C18—H18···Cg2i0.932.843.3942 (16)120
C3—H3···O1iii0.932.643.519 (2)157
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7···Cg1i0.982.923.7835 (16)148
C16—H16B···Cg1ii0.972.763.650 (2)153
C18—H18···Cg2i0.932.843.3942 (16)120
C3—H3···O1iii0.932.643.519 (2)157
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z.
 

Acknowledgements

EMM is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of Senior Research Fellowship. The authors are grateful to Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for single-crystal X-ray diffraction measurements.

References

First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCiganek, E. (1980). J. Org. Chem. 45, 1497–1505.  CrossRef CAS Web of Science Google Scholar
 First citationCox, J. R., Simpson, J. H. & Swager, T. M. (2013). J. Am. Chem. Soc. 135, 640–643.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationDe Luca, L., Giacomelli, G. & Taddei, M. (2001). J. Org. Chem. 66, 2534–2537.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKhalil, A. M., Berghot, M. A., Gouda, M. A. & Bialy, S. A. E. (2010). Monatsh. Chem. 141, 1353–1360.  Web of Science CrossRef CAS Google Scholar
 First citationMathew, E. M., Sithambaresan, M., Unnikrishnan, P. A. & Kurup, M. R. P. (2013). Acta Cryst. E69, o1165.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 70| Part 2| February 2014| Page o114
doi:10.1107/S1600536814000026
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